Ethyl 3-cyano-3-(3,4-dimethoxyphenyl)propionate | 40878-19-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Ethyl 3-cyano-3-(3,4-dimethoxyphenyl)propionate
• 英文别名: cyanoester；ethyl 3-cyano-3-(3,4-dimethoxyphenyl)-propionate；3-Cyano-3-(3,4-dimethoxyphenyl)propionsaeure-ethylester；2-(3',4'-Dimethoxybenzyl)cyanoacetataethylester；Ethyl 3-cyano-3-(3,4-dimethoxyphenyl)propanoate
• CAS: 40878-19-1
• 化学式: C₁₄H₁₇NO₄
• 分子量: 263.293
• InChiKey: UNQLSSYUCYRCDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  68.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 3-cyano-3-(3,4-dimethoxyphenyl)propionate 在 sodium tetrahydroborate 、 正丁基锂 、 Diisobutylalan 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 反应 4.0h， 以89%的产率得到cyanoalcohol
  参考文献：
  名称：

  A Convenient Synthesis of 3-Arylbutanolides and 3-Arylbutenolides

  摘要：

  A series of 3-aryl-substituted butenolides and butanolides has been prepared in a common short synthetic sequence from the corresponding aryl aldehydes. The 3-arylbutanolides are prepared by cyclisation of 3-aryl-3-cyano-1-propanols, obtained by selective reduction of 3-aryl-3-cyanopropionate esters, and are converted to 3-arylbutenolides by a sulfoxide or selenoxide elimination reaction.

  DOI：

  10.1080/00397919808004439
• 作为产物：
  描述：

  二乙基(3,4-dimethoxybenzylidene)丙二酸酯 、 氰化钾 以 甲醇 、 水 为溶剂， 生成 Ethyl 3-cyano-3-(3,4-dimethoxyphenyl)propionate
  参考文献：
  名称：

  Inhibition of cyclic adenosine-3',5'-monophosphate phosphodiesterase from vascular smooth muscle by rolipram analogs

  摘要：

  Rolipram [(R,S)-4-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-pyrrolidone] has been shown to inhibit selectively the cAMP phosphodiesterase (PDE) of vascular smooth muscle. In order to further explore the structural requirements for selective PDE inhibition, we synthesized a series of rolipram derivatives differently substituted either at the pyrrolidinone or at the aromatic ring. Among these compounds, rolipram was the most active compound. Semirigid analogues were prepared and used for an evaluation of the active conformation of rolipram. Structural comparison with two other potent and chemically different smooth muscle cAMP-PDE inhibitors, trequinsin and Ro 20-1724, allows us to propose a first topological model of the smooth muscle cAMP-PDE pharmacophore.

  DOI：

  10.1021/jm00127a009

文献信息

• Pyrrolidine compound and pharmaceutical use
  申请人：Eisai Co., Ltd.

  公开号：EP0381235A2

  公开（公告）日：1990-08-08

  A pyrrolidine compound having the formula and a pharmacologically acceptable salt thereof is disclosed. It is useful in the pharmaceutical field. in which X is hydrogen, a halogen, or a lower alkyl, Y is -(CH2)n-, n being zero, 1 or 2, -S(O)p-, p being zero, 1 or 2, -O-, or -NH- and R is phenyl, a substituent-having phenyl, naphtyl, a substituent-having naphthyl, a heteroaryl or a substituent-having heteroaryl.

  本发明公开了一种具有以下式子的吡咯烷化合物及其药理学上可接受的盐。 其中 X 是氢、卤素或低级烷基，Y 是-(CH2)n-，n 为零、1 或 2，-S(O)p-，p 为零、1 或 2，-O- 或-NH-，R 是苯基、具有苯基的取代基、萘基、具有萘基的取代基、杂芳基或具有杂芳基的取代基。
• Inhibition of cyclic adenosine-3',5'-monophosphate phosphodiesterase from vascular smooth muscle by rolipram analogs
  作者：Michel C. Marivet、Jean Jacques Bourguignon、Claire Lugnier、Andre Mann、Jean Claude Stoclet、Camille Georges Wermuth

  DOI：10.1021/jm00127a009

  日期：1989.7

  Rolipram [(R,S)-4-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-pyrrolidone] has been shown to inhibit selectively the cAMP phosphodiesterase (PDE) of vascular smooth muscle. In order to further explore the structural requirements for selective PDE inhibition, we synthesized a series of rolipram derivatives differently substituted either at the pyrrolidinone or at the aromatic ring. Among these compounds, rolipram was the most active compound. Semirigid analogues were prepared and used for an evaluation of the active conformation of rolipram. Structural comparison with two other potent and chemically different smooth muscle cAMP-PDE inhibitors, trequinsin and Ro 20-1724, allows us to propose a first topological model of the smooth muscle cAMP-PDE pharmacophore.
• MARIVET, MICHEL C.;BOURGUIGNON, JEAN-JACQUES;LUGNIER, CLAIRE;MANN, ANDRE;+, J. MED. CHEM., 32,(1989) N, C. 1450-1457
  作者：MARIVET, MICHEL C.、BOURGUIGNON, JEAN-JACQUES、LUGNIER, CLAIRE、MANN, ANDRE、+

  DOI：——

  日期：——
• US3958003A
  申请人：——

  公开号：US3958003A

  公开（公告）日：1976-05-18
• A Convenient Synthesis of 3-Arylbutanolides and 3-Arylbutenolides
  作者：J.-X. Gu、H. L. Holland

  DOI：10.1080/00397919808004439

  日期：1998.9

  A series of 3-aryl-substituted butenolides and butanolides has been prepared in a common short synthetic sequence from the corresponding aryl aldehydes. The 3-arylbutanolides are prepared by cyclisation of 3-aryl-3-cyano-1-propanols, obtained by selective reduction of 3-aryl-3-cyanopropionate esters, and are converted to 3-arylbutenolides by a sulfoxide or selenoxide elimination reaction.